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Seasons Vacation Rentals in Kissimmee

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    Travelers to Kissimmee are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    19 Matching Rentals in KissimmeeView all 6,789 rentals
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    Kissimmee, Florida, "Amazing Castle in the Sun"1 / 28
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    DORAL WOODS SECLUDED VILLA1 / 24
    (33)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Affordable and Luxurious Ground Floor Condo at Cane Island Resort1 / 23
    (29)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 101 / 34
    (23)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2017
    We absolutely LOVE this rental!!! House is beautiful, spacious, well maintained, in a perfect location. Very close to Disney World,Seaworld and Universal amusement parks. Within...
    Reviewed June 12, 2017
    The house was great but not sure if the pool was working properly but it was not a big deal. The house was very spacious and had more than enough room for everyone. The location...
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    About this property
    Welcome to our home on Seasons. It is a St Vincent model built by Park Square Homes and is 2765 Sq. Foot of Executive quality. It is a luxurious 5 Bedroom – 4 Bathroom Villa, which has 2 Master Suites and 3 other Bedrooms - which comfortably sleep 10 with ease, a Private Pool and spa plus a well...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Big Pool Villa with a Hot Tub - Several Great August & September Dates1 / 46
    (27)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 16, 2017
    What a FANTASTIC villa! Just got back from spending 2 weeks at Big Pool Villa and cannot praise it up enough.There were 8 adults and 4 children in our group. Bedroom...
    Reviewed March 17, 2017
    This house was amazing. It has everything you need. Jeanie was very helpful. I Will book this again. I could not have ask for anything more and the directions they gave us was...
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    About this property
    Aug/Sept 17 dates available now. Welcome! Our 6 bed 4.2 bath villa is where you want to be only 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street. Our villa is in the area known to locals as the Golden Mile. This villa has a stunning 40 foot...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    Enchanting Star Lake View House with Balcony, Pool, and Jacuzzi1 / 200
    (7)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Private Indoor Pool
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 15, 2017
    There were five adults and one child. We visited during the rainy season so that may have been the reason for the roaches. There weren't a lot but enough to keep us out of the...
    Reviewed February 11, 2017
    Ann, thanks for everything. Perfect location, great place! Very comfortable house.The house is well maintenance and quiet condo.
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    About this property
    This immaculate 4 bedroom, 3 bath, family vacation villa is ideally situated only 3 miles from Disney World! The villa overlooks a tranquil lake, a home to herons and other wildlife all year round, and from here it's a short journey to all the major attractions in and around Orlando. <BR><BR>The...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Affordable Luxury for Your Family Next to Disney1 / 33
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2017
    We stayed here for 7 nights for our trip to Disney and Universal Studios. The location was perfect - 20 minutes to Universal Studios and 10 minutes to Disney. The condo is...
    Reviewed August 25, 2016
    We have never rented a condo, so this was a new venture for us. In the past, we've stayed on Disney property, which is totally cramped and overpriced. When we stepped in to...
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    About this property
    Windsor Hills is an oasis only a mile from Disney World. Amenities include a huge pool with a water slide, clubhouse, playgrounds, exercise room, putting green, sports area, convenience store and shuttles to major attractions. AAA gives it a 3 diamond rating and units are in high demand. Our...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedroom Orlando Vacation Rental awesome locatio1 / 40
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2017
    When my family got to Kissimmee we had a rude awakening our logging had been cancelled I just so happen to open up the site and found Jim he had just had a cancellation and a...
    Reviewed April 25, 2016
    Coming from Canada you don't know what you have rented until you arrive. We were very very pleased with the service on line to book our stay. The house, grounds & pool were...
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    About this property
    Our executive villa at island club is one of the most sought after destination resort for families visiting the Orlando area. It has earned this reputation because it boasts one of the best location with Disney World just 4 miles away. So close you can "See the fireworks from your own back yard"....
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windsor Hills 3 Bedroom Condo located just 2 minutes from Disney1 / 11
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 12, 2017
    We rent a condo for a month every year so we have had a lot of experience,both good and bad. This was pretty good. We have stayed at Windsor Palms before so we knew the general...
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    About this property
    BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET in the Condo, FLAT SCREEN HDTV's ALL ROOMS, DVD PLAYERS, Private Washer/Dryer BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET...
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    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stunning Lake View 7 bdrms 5.5 baths(4 suites)1 / 40
    (29)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 2, 2017
    Brilliant house. Had a fantastic time while at the property. Very clean and tidy. The instructions from the owner were very clear and helpful
    Reviewed November 9, 2016
    The home we stayed in was well decorated. It had all the comforts of home. The kitchen was well stocked with everything you could possibly need. The only problem we had was the...
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    About this property
    Lake view private swimming pool and 6 miles away from Disney with excellent access to all of Orlando's Disney theme parks and golf courses, Harmony Villa is the perfect place for your vacation in Florida. Located on the peaceful and exclusive Seasons community in Kissimmee, our brand new furnished...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Indian Ridge 21571 / 15
    (13)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 26, 2013
    Wonderful location for our place. Great for the money! Yes older pool and home, but in great condition.
    Reviewed June 11, 2011
    Please bring or be prepared to buy cleaning supplies and garbage bags. There was a vacuum and broom with dust pan. You will need soap, paper towels, and tissues. There was only...
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    About this property
    This spacious Three bedroomed home is situated in a peaceful area on the popular Indian Ridge complex. Located only 3 miles for Disney World Resort area, this community features a community swimming pool, tennis courts, a children’s playground, and walking trail.The large Master bedroom has a queen...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedroom Pool Home & Spa - Orlando vacation rental1 / 20
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2014
    We spent more than two months last year in Seasons Blvd and it was a great experience. Jim was very helpful in every issue and solved problems promptly.. House was also great...
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    About this property
    Orlando vacation home with private pools located in select community of Seasons. This vacation homes are "the best option" for families that have 4-10 members, need a little privacy, and enjoy a private pool, garage, spacious patio areas in your own back yard. Looking to get away from the cold...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Regal Oaks, Old Town, Kissimmee1 / 20
    (36)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    • Balcony
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This house was everything we hoped for and more. It was my special birthday and the owner arranged for a bottle of champagne and a birthday card to be left really nice touch on...
    Reviewed April 20, 2017
    Just back from an amazing 3 week stay at Regal Oaks. It's the perfect location for the theme parks,shops bars and restaurants all within a few minutes walk. It's the first time...
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    About this property
    Our very well equipped, self catering, townhouse is located on the exclusive four star Regal Oaks, a fully managed resort with office and tourist information centre, at Old Town Kissimmee. Ideal for families or groups of up to 8 people. Regal Oaks is now a gated community and a resort offering a...
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    Location Information
    Kissimmee, Central Florida FL34746
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    15% off rates for 20161 / 31
    (18)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2016
    We stayed here the week of June 27, 2016. The house was as nice as the pictures, very spacious, clean, and worked well for our large group. No complaints. Highly recommended...
    Reviewed May 4, 2016
    The house was everything they said and showed. ... only 20 min from Disney. with almost no traffic .. close to super markets drug stores. take out and more.For the price it was...
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    About this property
    THIS DEAL IS NOT INCLUDED WITH ANY OTHER DEAL BEING OFFERED. ALL RATES ON HOME HAVE ALREADY BEEN DISCOUNTED BY 15%. NO PETS/ANIMALS ALLOWED. NO SMOKING ALLOWED. FREE - WIFI - FREE - PACK N PLAY AND FREE - HIGH CHAIR. Beautiful two story 6 bed 5.5 bath pool/spa home ( SLEEPS 12 PEOPLE)...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    15% off rates for 20161 / 32
    (15)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2016
    This vacation home really met my family needs! Mrs. Westlake was very accessible through the whole process. We paid to heat the pool and spa in the back yard and it was very...
    Reviewed March 19, 2014
    The house was spacious, clean and fulfilled all our needs; a 'crashing-pad'. The shortcut to the parks was a huge time-saver!The only fault and the reason for 4/5 stars is the...
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    About this property
    2881 Heated Square Feet 4213 total area of property THIS DEAL IS NOT INCLUDED WITH ANY OTHER DEAL BEING OFFERED. ALL RATES ON THIS HOME HAVE ALREADY BEEN DISCOUNTED BY 15% . NO PETS/ANIMALS ALLOWED NO SMOKING ALLOWED FREE WIFI FREE - FREE PACK N PLAY AND FREE HIGH CHAIR GAME ROOM WITH...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    15% off rates for 20161 / 20
    (13)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Outdoor Dining Area
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 17, 2015
    We enjoyed the house very much. Our family included my wife and me and 2 sons and daughter and their families. The house was very comfort and met our needs and expectations...
    Reviewed December 4, 2014
    The location was perfect for the typical Florida activities; Disney, Universal Studios and the beaches. Very close to many restaurants and grocery stores. The resort its self...
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    About this property
    THIS DEAL IS NOT INCLUDED WITH ANY OTHER DEAL BEING OFFERED. ALL RATES ON HOME HAVE ALREADY BEEN DISCOUNTED BY 15%. NO PETS/ANIMALS ALLOWED. NO SMOKING ALLOWED. FREE - WIFI - FREE - PACK N PLAY AND FREE - HIGH CHAIR. Beautiful two story 6 bed 5.5 bath pool/spa home ( SLEEPS 12 PEOPLE)...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lindfields has been a firm favorite amongst the neighborhoods along the Disney World Resort area. Within 5 miles of Disney World, its popularity boasts many facets including easy access to shops, restaurants and attractions. A quick hop over to I-4 will take you over to many more attractions that...
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    Kissimmee, Central Florida 34747
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    15% off rates  for 20161 / 23
    (8)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2016
    Loved the villa, spacious, clean, local to Disney. Housekeeping team of Mr & Mrs Westlake extremely easy to deal with. There are plenty of extra's, and all easy on the eye.I...
    Reviewed August 21, 2015
    We had an amazing 10 days, this house is perfect for 2 families!! 2 master suites!!! loved it. within 15 minutes to all the parks!
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    About this property
    2136 Heated Square Feet 3104 total area of property THIS DEAL IS NOT INCLUDED WITH ANY OTHER DEAL BEING OFFERED WITH ANY OTHER HOMES. RATES ON THIS HOME HAVE ALREADY BEEN DISCOUNTED BY 15%. NO PETS/ANIMALS ALLOWED - NO SMOKING ALLOWED FREE WIFI, FREE - PACK N PLAY AND FREE - HIGH CHAIR...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bed 3 Bath Townhouse - Windsor Hills Resort1 / 32
    (18)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    • Terrace
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 7, 2016
    We recently stayed in this wonderful 3 bed 3 bath Townhouse on Windsor Hill Resort. We had an amazing holiday and the Townhouse was beautiful, very homely and very well...
    Reviewed November 13, 2016
    So glad we chose this townhouse, it was absolutely perfect. Everything we needed was at hand. Very spacious and only a couple of minutes walk to the clubhouse and main pool...
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    About this property
    3 Bed 3 Bath Townhouse. Fabulous 3 bedroom, 3 bathroom townhouse on Windsor Hills Resort. This home is extremely close to the fantstic resort lagoon style zero entry pool and clubhouse with all of its amenities including movie theatre and general store. With our own west facing splash pool...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    10.4 miles from Kissimmee
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    • Local time: 03:19 AM (EDT)
    • Peak travel: March - April
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